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2-methyl butyraldehyde

Chemical Structure

General Material Information

Preferred name 2-methyl butyraldehyde
Trivial Name 2-Methylbutanal
Short Description 2-methylbutyraldehyde
Formula C5 H10 O
CAS Number 96-17-3
Deleted CAS Number 57456-98-1
FEMA Number 2691
Flavis Number 5.049
ECHA Number 202-485-6
FDA UNII 47H597M1YY
Nikkaji Number J35.111C
Beilstein Number 1633540
MDL MFCD00006984
COE Number 575
xLogP3-AA 1.10 (est)
Bio Activity Summary External link
NMR Predictor External link
JECFA Food Flavoring 254 2-methylbutyraldehyde
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm 96-17-3 ; 2-METHYLBUTYRALDEHYDE
Synonyms
  • acetaldehyde, ethylmethyl-
  • butanal, 2-methyl-
  • butyraldehyde, 2-methyl-
  • 2-ethyl propanal
  • 2-ethylpropanal
  • 2-formyl butane
  • 2-methyl butanal
  • alpha- methyl butanal
  • alpha- methyl butyraldehyde
  • nat.2-methyl butyraldehyde
  • 2-methyl butyraldehyde natural
  • alpha- methyl butyric aldehyde
  • methyl ethyl acetaldehyde
  • 2-methyl-1-butanal
  • a-2-methyl-N-butanal
  • alpha-2-methyl-N-butanal
  • 2-methylbutanal
  • a- methylbutanal
  • 2-methylbutyraldehyde
  • a- methylbutyraldehyde
  • 2-methylbutyraldehyde 99%, (naturals)
  • 2-methylbutyraldehyde natural
  • 2-methylbutyric aldehyde
  • a- methylbutyric aldehyde
  • alpha- methylbutyric aldehyde
  • methylethyl acetaldehyde
  • methylethylacetaldehyde
  • Butyraldehyde, α-methyl-
  • 2-Methylbutanal
  • α-Methylbutanal
  • α-Methylbutyraldehyde
  • 2-Methylbutyraldehyde
  • 2-Methylbutyric aldehyde
  • α-Methylbutyric aldehyde
  • 2-Formylbutane
  • α-Methyl-n-butanal
  • 2-Ethylpropanal
  • (RS)-2-Methylbutanal
  • (±)-2-Methylbutanal
  • NSC 77077
  • (±)-2-Methylbutyraldehyde

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Literature & References

Leffingwell:Chirality or Article
2-methylbutanal
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:96-17-3
Pubchem (cid):7284
Pubchem (sid):134972369
Flavornet:96-17-3
Pherobase:View
Publications by Info
Volatile Flavor Components in Bogyojosaeng and Suhong Cultivars of Strawberry (Fragaria ananassa Duch.)
Publications by PubMed
Identification and Characterization of the Aroma-Impact Components of Thai Fish Sauce.
Severe drought stress is affecting selected primary metabolites, polyphenols, and volatile metabolites in grapevine leaves (Vitis vinifera cv. Pinot noir).
Variation of volatile compounds among wheat varieties and landraces.
Influence of storage on volatile profiles in roasted almonds (Prunus dulcis).
Evaluation of volatile aldehydes as discriminating parameters in quality vinegars with protected European geographical indication.
OH-initiated photooxidations of 1-pentene and 2-methyl-2-propen-1-ol: mechanism and yields of the primary carbonyl products.
Characterisation of aroma profiles of commercial soy sauce by odour activity value and omission test.
Quantitative volatile compound profiles in fungal cultures of three different Fusarium graminearum chemotypes.
Lactose-hydrolyzed milk is more prone to chemical changes during storage than conventional ultra-high-temperature (UHT) milk.
Characterization of important odorants in steamed male Chinese mitten crab (Eriocheir sinensis) using gas chromatography-mass spectrometry-olfactometry.
Characterization of volatile aroma compounds in different brewing barley cultivars.
Volatile constituents of commercial imported and domestic black-ripe table olives (Olea europaea).
2-methylbutanal, a volatile biomarker, for non-invasive surveillance of Proteus.
Characterization of protein hydrolysis and odor-active compounds of fish sauce inoculated with Virgibacillus sp. SK37 under reduced salt content.
Characterization of the aroma signature of styrian pumpkin seed oil ( Cucurbita pepo subsp. pepo var. Styriaca) by molecular sensory science.
[Difference of volatile constituents contained in female and male flowers of Trichosanthes kirilowii by HS-SPME-GC-MS].
Thermochemistry of radicals formed by hydrogen abstraction from 1-butanol, 2-methyl-1-propanol, and butanal.
Metabolic profiling of Lactococcus lactis under different culture conditions.
Differentiation of fresh and frozen/thawed fish, European sea bass (Dicentrarchus labrax), gilthead seabream (Sparus aurata), cod (Gadus morhua) and salmon (Salmo salar), using volatile compounds by SPME/GC/MS.
Headspace analysis of Italian and New Zealand parmesan cheeses.
Tentative identification of volatile flavor compounds in commercial Budu, a Malaysian fish sauce, using GC-MS.
Biosynthesis of rhodiocyanosides in Lotus japonicus: rhodiocyanoside A is synthesized from (Z)-2-methylbutanaloxime via 2-methyl-2-butenenitrile.
Statistical thermodynamics of 1-butanol, 2-methyl-1-propanol, and butanal.
Screening for emphysema via exhaled volatile organic compounds.
Identification of chemical markers for the sensory shelf-life of saveloy.
Sensory and physicochemical evolution of tropical cooked peeled shrimp inoculated by Brochothrix thermosphacta and Lactococcus piscium CNCM I-4031 during storage at 8°C.
Use of Tetragenococcus halophilus as a starter culture for flavor improvement in fish sauce fermentation.
Effect of enzyme activity and frozen storage on jalapeño pepper volatiles by selected ion flow tube-mass spectrometry.
Biosynthesis of the cyanogenic glucosides linamarin and lotaustralin in cassava: isolation, biochemical characterization, and expression pattern of CYP71E7, the oxime-metabolizing cytochrome P450 enzyme.
Effects of lipase, lipoxygenase, peroxidase and free fatty acids on volatile compound found in boiled buckwheat noodles.
Influence of pre-cure freezing on the profile of volatile compounds during the processing of Iberian hams.
Low-temperature catalytic oxidation of aldehyde mixtures using wood fly ash: kinetics, mechanism, and effect of ozone.
Flavor variability and flavor stability of U.S.-produced whole milk powder.
Kinetic modeling of the generation of 2- and 3-methylbutanal in a heated extract of beef liver.
Release of volatile organic compounds from the lung cancer cell line NCI-H2087 in vitro.
Super chilling enhances preservation of the freshness of salted egg yolk during long-term storage.
Characterization of the most odor-active compounds in an American Bourbon whisky by application of the aroma extract dilution analysis.
Biofiltration kinetics of a gaseous aldehyde mixture using a synthetic matrix.
Characterization of the key aroma compounds in soy sauce using approaches of molecular sensory science.
An assessment of the role played by some oxidation-related aldehydes in wine aroma.
Quality and flavour stability of coffee substitute prepared by extrusion of wheat germ and chicory roots.
Permeabilization and lysis induced by bacteriocins and its effect on aldehyde formation by Lactococcus lactis.
Identification of the key aroma compounds in cocoa powder based on molecular sensory correlations.
Critical aspects of the determination of pentafluorobenzyl derivatives of aldehydes by gas chromatography with electron-capture or mass spectrometric detection: Validation of an optimized strategy for the determination of oxygen-related odor-active aldehydes in wine.
Electrophysiological and behavioral responses of a parasitic wasp to plant volatiles induced by two leaf miner species.
Cell membrane damage induced by lacticin 3147 enhances aldehyde formation in Lactococcus lactis IFPL730.
Volatiles released from bean plants in response to agromyzid flies.
Analysis of volatile compounds from various types of barley cultivars.
Interaction of soluble peptides and proteins from skeletal muscle with volatile compounds in model systems as affected by curing agents.
Effect of the type of frying culinary fat on volatile compounds isolated in fried pork loin chops by using SPME-GC-MS.
Branched-chain fatty acid biosynthesis in a branched-chain amino acid aminotransferase mutant of Staphylococcus carnosus.
Identification by gas chromatography-mass spectrometry of the volatile organic compounds emitted from the wood-rotting fungi Serpula lacrymans and Coniophora puteana, and from Pinus sylvestris timber.
Enhancement of 2-methylbutanal formation in cheese by using a fluorescently tagged Lacticin 3147 producing Lactococcus lactis strain.
On-line monitoring of important organoleptic methyl-branched aldehydes during batch fermentation of starter culture Staphylococcus xylosus reveal new insight into their production in a model fermentation.
Analysis of aldehydes in beer using solid-phase microextraction with on-fiber derivatization and gas chromatography/mass spectrometry.
Effect of pH and temperature on the kinetics of odor oxidation using chlorine dioxide.
Interactions of soluble peptides and proteins from skeletal muscle on the release of volatile compounds.
Lacticin 3147 favours isoleucine transamination by Lactococcus lactis IFPL359 in a cheese-model system.
Solvent-free asymmetric olefin hydroformylation catalyzed by highly cross-linked polystyrene-supported (R,S)-BINAPHOS-Rh(I) complex.
Quantification of aroma compounds in Parmigiano Reggiano cheese by a dynamic headspace gas chromatography-mass spectrometry technique and calculation of odor activity value.
NTP Toxicology and Carcinogenesis Studies of Isobutyraldehyde (CAS No. 78-84-2) in F344/N Rats and B6C3F1 Mice (Inhalation Studies).
Volatile compounds of headspace gas in the Japanese fish sauce ishiru.
Volatile compounds in Hispánico cheese manufactured using a mesophilic starter, a thermophilic starter, and bacteriocin-producing Lactococcus lactis subsp. lactis INIA 415.
Effect of cultivar and storage time on the volatile flavor components of baked potato.
Characterization of Ypr1p from Saccharomyces cerevisiae as a 2-methylbutyraldehyde reductase.
Identification of distinctive volatile compounds in fish sauce.
Quantitation of odor-active compounds in rye flour and rye sourdough using stable isotope dilution assays.
Identification of aroma compounds in Parmigiano-Reggiano cheese by gas chromatography/olfactometry.
Wet scrubber analysis of volatile organic compound removal in the rendering industry.
Use of gas chromatography-olfactometry to identify key odorant compounds in dark chocolate. Comparison of samples before and after conching.
Relationships between antioxidant activity, color, and flavor compounds of crystal malt extracts.
Formation of volatile compounds during heating of spice paprika (Capsicum annuum) powder.
Contribution of 3-methylthiopropionaldehyde to the worty flavor of alcohol-free beers.
Volatile components of roots, stems, leaves, and flowers of Echinacea species.
Quantification and sensory studies of character impact odorants of different soybean lecithins.
Volatile flavor components of rice cakes.
The biosynthesis of cyanogenic glucosides in seedlings of cassava (Manihot esculenta Crantz).
Catalysis by cytochrome P-450 of an oxidative reaction in xenobiotic aldehyde metabolism: deformylation with olefin formation.
Poisoning by 2-methylbutyraldehyde (isovaleraldehyde).

Other Information

(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
FDA Substances Added to Food (formerly EAFUS):View
CHEBI:View
CHEMBL:View
KEGG (GenomeNet):C02223
HMDB (The Human Metabolome Database):HMDB31526
FooDB:FDB008127
YMDB (Yeast Metabolome Database):YMDB00485
Export Tariff Code:2912.19.5000
Typical G.C.
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 86.133903503418
Specific gravity @ 25 °C
Pounds per Gallon 6.657 to 6.74
Refractive Index 1.386 to 1.394 @ 20 °C
Boiling Point 90 to 93°C @ 760 mm Hg
Acid Value 5 max KOH/g
Vapor Pressure 49.317001 mmHg @ 25 °C
Vapor Density 2.9
Flash Point TCC Value 4.44 °C TCC
logP (o/w) 1.267 est
Solubility
alcohol Yes
water, 1.123e+004 mg/L @ 25 °C (est) Yes
Stability
alkalis Unspecified

Organoleptic Properties

Odor Type: Cocoa
musty, cocoa, phenolic, coffee, nutty, malty, fermented, fatty, alcoholic, chocolate
Odor strength high , recommend smelling in a 1.00 % solution or less
Substantivity > 1 hour(s) at 100.00 %
Luebke, William tgsc, (2021) At 1.00 % in dipropylene glycol. musty cocoa phenolic coffee nutty malty fermented fatty alcoholic
Mosciano, Gerard P&F 23, No. 1, 33, (1998) Musty, chocolate, nutty, furfural and iaovaleraldehyde-like with malty and fermented nuances
Flavor Type: Fusel
musty, rummy, nutty, cereal, caramellic, fruity
Luebke, William tgsc, (2021) Musty fusel rummy nutty cereal caramellic fruity cocoa
Mosciano, Gerard P&F 23, No. 1, 33, (1998) At 10.00 ppm. Musty, furfural and rummy, with nutty and cereal notes, and caramel and fruity undernotes
Useful for chocolate, cocoa, mocha/coffee flavors. Strong, cocoa powder notes

Occurrences

Potential Uses

Applications
Flavoring purposes Apple , Banana , Berry mixed berry , Bread , Caramel , Chocolate cocoa , Coffee , Grape , Malt , Olive , Papaya , Rum , Tomato , Tropical , Wine
Cosmetic purposes Perfuming agents

Safety Information

Safety information

Preferred SDS: View
European information :
Most important hazard(s):
Xi - Irritant
R 11 - Highly flammable.
R 36/37/38 - Irritating to eyes, respiratory system, and skin.
R 53 - May cause long-term adverse effects in the aquatic wnvironment.
S 02 - Keep out of the reach of children.
S 16 - Keep away from sources of ignition - No Smoking.
S 24/25 - Avoid contact with skin and eyes.
S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S 36/37/39 - Wear suitable clothing, gloves and eye/face protection.
S 61 - Avoid release to the environment. Refer to special instructions/safety data sheet.
Hazards identification
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
Pictogram
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
oral-rat LD50 6400 mg/kg
Food and Chemical Toxicology. Vol. 20, Pg. 739, 1982.

Dermal Toxicity:
skin-rabbit LD50 5730 ul/kg
Union Carbide Data Sheet. Vol. 10/5/1972

skin-guinea pig LD50 > 20000 mg/kg
Food and Chemical Toxicology. Vol. 20, Pg. 739, 1982.

Inhalation Toxicity:
inhalation-rat LC50 14000 ppm/4H
Union Carbide Data Sheet. Vol. 10/5/1972

Safety in use information

Category:
flavor and fragrance agents
RIFM Fragrance Material Safety Assessment: Search
IFRA Code of Practice Notification of the 49th Amendment to the IFRA Code of Practice
Recommendation for 2-methyl butyraldehyde usage levels up to:
0.3000 % in the fragrance concentrate.
Structure Class: I
Use levels for FEMA GRAS flavoring substances on which the FEMA Expert Panel based its judgments that the substances are generally recognized as safe (GRAS).
The Expert Panel also publishes separate extensive reviews of scientific information on all FEMA GRAS flavoring substances and can be found at FEMA Flavor Ingredient Library
publication number: 3
Click here to view publication 3
average usual ppmaverage maximum ppm
baked goods: -5.70000
beverages(nonalcoholic): 1.500002.00000
beverages(alcoholic): --
breakfast cereal: --
cheese: --
chewing gum: --
condiments / relishes: --
confectionery froastings: --
egg products: --
fats / oils: --
fish products: --
frozen dairy: 2.000008.00000
fruit ices: 2.000008.00000
gelatins / puddings: --
granulated sugar: --
gravies: --
hard candy: -6.60000
imitation dairy: --
instant coffee / tea: --
jams / jellies: --
meat products: --
milk products: --
nut products: --
other grains: --
poultry: --
processed fruits: --
processed vegetables: --
reconstituted vegetables: --
seasonings / flavors: --
snack foods: --
soft candy: --
soups: --
sugar substitutes: --
sweet sauces: --

Safety references

European Food Safety Authority (EFSA) reference(s):

Flavouring Group Evaluation 3, Revision 1 (FGE.03Rev1): Acetals of branched- and straight-chain aliphatic saturated primary alcohols and branched- and straight-chain saturated or unsaturated aldehydes, an ester of a hemiacetal and an orthoester of formic acid, from chemical groups 1, 2 & 4 Commission Regulation (EC) No 1565/2000 of 18 July 2000) [1] - Scientific Opinion of the Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in contact with Food (AFC)on a request from the Commission
View page or View pdf

EPI System: View
Chemical Carcinogenesis Research Information System:Search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):96-17-3
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :7284
National Institute of Allergy and Infectious Diseases:Data
WISER:UN 1989
WGK Germany:1
2-methylbutanal
Chemidplus:0000096173
RTECS:ES3400000 for cas# 96-17-3